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Expedient Pd‐Catalyzed α‐Arylation towards Dibenzoxepinones: Pivotal Manske's Ketone for the Formal Synthesis of Cularine Alkaloids
Author(s) -
Deichert Julie A.,
Mizufune Hideya,
Patel Jignesh J.,
Hurst Timothy E.,
Maheta Ashish,
Kitching Matthew O.,
Ross Avena C.,
Snieckus Victor
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000424
Subject(s) - chemistry , ketone , catalysis , formal synthesis , total synthesis , xanthone , ring (chemistry) , combinatorial chemistry , methyl ketone , stereochemistry , organic chemistry
The general synthesis of diversely substituted dibenzoxepinones by a combined Pd‐catalyzed α‐arylation and S N Ar strategy is reported and applied to the synthesis of Manske's ketone, a key intermediate en route to the total synthesis of cularine alkaloids. In the course of this work, an unanticipated ring contraction reaction to a xanthone was observed and serves as a caveat for the conditions of the widely used α‐arylation reaction.